Planta Med 2012; 78 - PK15
DOI: 10.1055/s-0032-1321331

Towards the biomimetic synthesis of lodopyridone

N Barbahn 1, L Evanno 1, E Poupon 1
  • 1Université Paris-Sud, Laboratoire de Pharmacognosie associé au CNRS, UMR 8076 BioCIS, LabEx LERMIT, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry Cedex, France

Lodopyridone is an alkaloid isolated in 2009 from the marine actinomycete Saccharomonospora sp. collected in sediments of the submarine canyon of La Jolla in the United States.1 The molecule contains three nitrogen heterocycles: i- a chlorinated quinoline, ii- a thiazole and iii- a pyridone.

This polyheterocyclic structure rather surprising at first for a natural substance is actually probably a modified tetrapeptide. The 4-pyridone cycle found in lodopyridone is quite uncommon in natural substances, and to date, only about twenty molecules containing this framework have been described. To realize the total synthesis, a biomimetic approach is privileged based on our biogenesis hypothesis and will be presented.

1) K. N. Maloney, J. B. MacMillan, C. A. Kauffman, P. R. Jensen, A. G. DiPasquale, A. L. Rheingold, W. Fenical, Org. Lett., 2009, 11, 5422–5424.